Trifluoroacetic acid → 5-fluoro-3-{[6-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamino]methyl}-1-methyl-1H-pyridin-2-one

HRID 509984ノート

反応式

HRID 509984 の反応式
[F:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([CH3:19])[CH:17]=2)[NH:12][CH:11]=1.[F:20][C:21]1[CH:22]=[C:23]([CH:29]=O)[C:24](=[O:28])[N:25]([CH3:27])[CH:26]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[F:20][C:21]1[CH:22]=[C:23]([CH2:29][NH:8][C:6]2[CH:5]=[CH:4][C:3]([CH2:9][C:10]3[C:18]4[C:13](=[N:14][CH:15]=[C:16]([CH3:19])[CH:17]=4)[NH:12][CH:11]=3)=[C:2]([F:1])[N:7]=2)[C:24](=[O:28])[N:25]([CH3:27])[CH:26]=1

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 582592126-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamineHCID 582594345-Fluoro-1-methyl-2-oxo-1,2-dihydro-pyridine-3-carbaldehyde

生成物 1

HCID 672020755-fluoro-3-{[6-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamino]methyl}-1-methyl-1H-pyridin-2-one収率 50.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

To 6-fluoro-5-(5-methyl-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyridin-2-ylamine (137, 3.99 g, 15.59 mmol) and 5-fluoro-1-methyl-2-oxo-1,2-dihydro-pyridine-3-carbaldehyde (33, 2.66 g, 17.15 mmol) in 50 mL of acetonitrile, triethylsilane (9.96 mL, 62.4 mmol) and trifluoroacetic acid (4.80 mL, 62.4 mmol) were added. The reaction was stirred at 80° C. for several hours, then concentrated under vacuum and the residue was taken up in ethyl acetate and poured into aqueous potassium carbonate. The organic layer was separated, concentrated under vacuum, and the residue purified by silica gel column chromatography, eluting with 0-5% methanol in dichloromethane. Appropriate fractions were combined and concentrated under vacuum, and the residue triturated with methanol to provide the desired compound (P-2156, 3.1 g, 7.84 mmol, 50.3% yield).

後処理

  1. concentrationconcentrated under vacuum
  2. additionpoured into aqueous potassium carbonate
  3. customThe organic layer was separated
  4. concentrationconcentrated under vacuum
  5. customthe residue purified by silica gel column chromatography
  6. washeluting with 0-5% methanol in dichloromethane
  7. concentrationconcentrated under vacuum
  8. customthe residue triturated with methanol

出典と根拠

ORDレコード
ord-3e3b0d8ffbf34d9aa3596efbd81b7c42
出典データセット
uspto-grants-2015_08
特許番号
US09096593B2

反応ノート

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